Ethanol → 2-Ethoxy-5-methoxybenzoic acid

HRID 228623

Reaction equation

HRID 228623 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:7]([C:8]([OH:10])=[O:9])[C:6]([OH:12])=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[CH2:17](O)[CH3:18]>>[CH2:17]([O:12][C:6]1[C:7](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[C:8]([OH:10])=[O:9])[CH3:18]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 757875-Methoxysalicylic Acid

Product 1

HCID 189545742-Ethoxy-5-methoxybenzoic acidYield 58%

Procedure

5-Methoxysalicylic acid (2.00 g) was suspended in ethanol (28 ml), and thionyl chloride (2.11 g) was gradually added dropwise to the suspension. Thereafter, the mixture was heated under reflux for 2 hr. The solvent was removed therefrom by distillation under the reduced pressure. Water was added to the residue, and the mixture was neutralized with a 20% aqueous sodium hydroxide solution and was then extracted with chloroform. The chloroform layer was then washed with water and saturated brine and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give ethyl 5-methoxysalicylic acid (1.37 g, yield 58%).

Workup

  1. temperatureThereafter, the mixture was heated
  2. temperatureunder reflux for 2 hr
  3. customThe solvent was removed
  4. distillationby distillation under the reduced pressure
  5. additionWater was added to the residue
  6. extractionwas then extracted with chloroform
  7. washThe chloroform layer was then washed with water and saturated brine
  8. dry with materialwas dried over anhydrous sodium sulfate
  9. customThe solvent was removed
  10. distillationby distillation under the reduced pressure
  11. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-4bfdb284ec3d478d801c03eb3cf59f4e
Source dataset
uspto-grants-2009_07
Patent number
US07560558B2

Linked notes

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